7. Dermontti Dawson

Dermontti Dawson was a Pittsburgh Steelers player and earned more than $25 million. After retirement he lost his cash quickly and didn’t have much left. He started off as a real estate developer after his NFL career. His investments didn’t pull through. Dawson ended up filing bankruptcy in 2010. His liabilities were a staggering $69.659 million versus assets totaling at $1.417 million.

PHOTO: Hawk Eyes| Flickr

Dawson is now one of the owners of Washington Wild Things, they are a member of the East Division of Frontier League. It is a private baseball league that is not affiliated with MLB. He did some coaching roles for Steelers and Cincinnati Bengals. Currently he works as a sales executive for a promotional products company.